It seems to me that there are two distinct things which the English word 'deceptive' describes:
Your formalism is of the first sense, which is why it's unintuitive that it does not take Bob's beliefs into account.
Following is the outline of a simple formalism for the second sense:
I don't think any one formalism can cover both senses. For one thing, it would need to represent the four possible states of "deceptiveness" as a binary "deceptive" property.
I think that it might be best to consider different terms to describe the two different senses of "deceptive."
I absolutely agree that writing assignments are effective. What I don't think is effective is grading longer submissions higher.